Did you select the delayed start option on the service?  I have found that necessary in Windows 7/Windows server 2008 r2 and later

Carter Browne
cbrowne@cbcs-usa.com

On 9/12/2014 12:57 PM, John Smith wrote:

Running stunnel 5.03 on Windows 2008 R2.

Everything is installed and working fine. I can even start/stop the service no problem... (Pretty sure the service is set to start Automatically)

When I reboot my server stunnel service shows as started but nothing gets logged and none of my connections work. Once I restart the service through service manager, everything works. So on startup it doesn't seem to run...

This only happens if i reboot the machine.

I also asked the same question here: http://serverfault.com/questions/627932/stunnel-as-windows-service-doesnt-start-on-reboot

Output of my logs proving it works.

2014.09.11 15:57:48 LOG5[1612]: stunnel 5.03 on x86-pc-msvc-1500 platform
2014.09.11 15:57:48 LOG5[1612]: Compiled/running with OpenSSL 1.0.1i-fips 6 Aug 2014
2014.09.11 15:57:48 LOG5[1612]: Threading:WIN32 Sockets:SELECT,IPv6 SSL:ENGINE,OCSP,FIPS
2014.09.11 15:57:48 LOG5[1612]: Reading configuration from file stunnel.conf
2014.09.11 15:57:48 LOG5[1612]: FIPS mode disabled
2014.09.11 15:57:49 LOG5[1612]: Configuration successful

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